ES2437149T3 - Agentes supresores del receptor de andrógenos - Google Patents
Agentes supresores del receptor de andrógenos Download PDFInfo
- Publication number
- ES2437149T3 ES2437149T3 ES09712693.2T ES09712693T ES2437149T3 ES 2437149 T3 ES2437149 T3 ES 2437149T3 ES 09712693 T ES09712693 T ES 09712693T ES 2437149 T3 ES2437149 T3 ES 2437149T3
- Authority
- ES
- Spain
- Prior art keywords
- benzylidene
- hydroxy
- methyl
- thiazolidine
- dione
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 239000003795 chemical substances by application Substances 0.000 title description 67
- 102000001307 androgen receptors Human genes 0.000 title description 36
- 108010080146 androgen receptors Proteins 0.000 title description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 108
- -1 amino, methoxy, ethoxy, nitro, phenyl Chemical group 0.000 claims abstract description 60
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 16
- 125000001475 halogen functional group Chemical group 0.000 claims abstract description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 238000011282 treatment Methods 0.000 claims description 49
- 206010028980 Neoplasm Diseases 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 43
- 206010060862 Prostate cancer Diseases 0.000 claims description 31
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims description 31
- 201000011510 cancer Diseases 0.000 claims description 26
- 239000002207 metabolite Substances 0.000 claims description 12
- 239000003814 drug Substances 0.000 claims description 9
- 230000002401 inhibitory effect Effects 0.000 claims description 6
- MADFJWDIMPOGOZ-UHFFFAOYSA-N 5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=C(C(O)=CC=2)C(F)(F)F)C(=O)N1CC1(C)CCCCC1 MADFJWDIMPOGOZ-UHFFFAOYSA-N 0.000 claims description 5
- ONYSVVZWJKKNPC-UHFFFAOYSA-N 5-[(4-hydroxy-3-nitrophenyl)methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=C(C(O)=CC=2)[N+]([O-])=O)C(=O)N1CC1(C)CCCCC1 ONYSVVZWJKKNPC-UHFFFAOYSA-N 0.000 claims description 4
- FRFXZAJIYPSMOV-UHFFFAOYSA-N 3-[(4-benzoylphenyl)methyl]-5-[(3-bromo-4-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)C(=O)S1 FRFXZAJIYPSMOV-UHFFFAOYSA-N 0.000 claims description 3
- UCLSLPCAMXFWKO-UHFFFAOYSA-N 4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]benzonitrile Chemical compound O=C1SC(=CC=2C=CC(=CC=2)C#N)C(=O)N1CC1(C)CCCCC1 UCLSLPCAMXFWKO-UHFFFAOYSA-N 0.000 claims description 3
- DOSUTQGEEFNBCL-UHFFFAOYSA-N 4-[[5-[(3-bromo-4-hydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]benzonitrile Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CC=2C=CC(=CC=2)C#N)C(=O)S1 DOSUTQGEEFNBCL-UHFFFAOYSA-N 0.000 claims description 3
- FANMQRSNMHKZCR-UHFFFAOYSA-N n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]-4-nitro-3-(trifluoromethyl)benzenesulfonamide Chemical compound O=C1SC(=CC=2C=CC(NS(=O)(=O)C=3C=C(C(=CC=3)[N+]([O-])=O)C(F)(F)F)=CC=2)C(=O)N1CC1(C)CCCCC1 FANMQRSNMHKZCR-UHFFFAOYSA-N 0.000 claims description 3
- TWLXALMZQJPFFI-UHFFFAOYSA-N n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]-4-nitrobenzenesulfonamide Chemical compound O=C1SC(=CC=2C=CC(NS(=O)(=O)C=3C=CC(=CC=3)[N+]([O-])=O)=CC=2)C(=O)N1CC1(C)CCCCC1 TWLXALMZQJPFFI-UHFFFAOYSA-N 0.000 claims description 3
- VYUHKUNAKDDQSR-UHFFFAOYSA-N n-[4-[[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]sulfamoyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1C=C1C(=O)N(CC2(C)CCCCC2)C(=O)S1 VYUHKUNAKDDQSR-UHFFFAOYSA-N 0.000 claims description 3
- LLHBJQRBCGKMSK-UHFFFAOYSA-N 2,2,2-trichloro-n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]acetamide Chemical compound O=C1SC(=CC=2C=CC(NC(=O)C(Cl)(Cl)Cl)=CC=2)C(=O)N1CC1(C)CCCCC1 LLHBJQRBCGKMSK-UHFFFAOYSA-N 0.000 claims description 2
- NYFBOEMIBANBHT-UHFFFAOYSA-N 2-[4-[[5-[(3-bromo-4-hydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]phenyl]benzonitrile Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C#N)C(=O)S1 NYFBOEMIBANBHT-UHFFFAOYSA-N 0.000 claims description 2
- JAKZEAMTAGBGQX-UHFFFAOYSA-N 2-[4-[[5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]methyl]phenyl]benzonitrile Chemical compound C1=C(C(F)(F)F)C(O)=CC=C1C=C1C(=O)N(CC=2C=CC(=CC=2)C=2C(=CC=CC=2)C#N)C(=O)S1 JAKZEAMTAGBGQX-UHFFFAOYSA-N 0.000 claims description 2
- KWBRFMNOQNGZSG-UHFFFAOYSA-N 2-methoxy-n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]-4-nitrobenzenesulfonamide Chemical compound COC1=CC([N+]([O-])=O)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1C=C1C(=O)N(CC2(C)CCCCC2)C(=O)S1 KWBRFMNOQNGZSG-UHFFFAOYSA-N 0.000 claims description 2
- SDZSWAHMMVQIJS-UHFFFAOYSA-N 3-[(1-methylcyclohexyl)methyl]-5-[(4-nitrophenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=CC(=CC=2)[N+]([O-])=O)C(=O)N1CC1(C)CCCCC1 SDZSWAHMMVQIJS-UHFFFAOYSA-N 0.000 claims description 2
- ZALUHLFAOREUKE-UHFFFAOYSA-N 3-[(1-methylcyclohexyl)methyl]-5-[[4-(trifluoromethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=CC(OC(F)(F)F)=CC=2)C(=O)N1CC1(C)CCCCC1 ZALUHLFAOREUKE-UHFFFAOYSA-N 0.000 claims description 2
- LWKDIZMZEIWNED-UHFFFAOYSA-N 3-[(3-chloro-5-fluorophenyl)methyl]-5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C(F)(F)F)C(O)=CC=C1C=C1C(=O)N(CC=2C=C(Cl)C=C(F)C=2)C(=O)S1 LWKDIZMZEIWNED-UHFFFAOYSA-N 0.000 claims description 2
- XIZBNMHUCDHFOS-UHFFFAOYSA-N 3-[(4-benzoylphenyl)methyl]-5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(C(F)(F)F)C(O)=CC=C1C=C1C(=O)N(CC=2C=CC(=CC=2)C(=O)C=2C=CC=CC=2)C(=O)S1 XIZBNMHUCDHFOS-UHFFFAOYSA-N 0.000 claims description 2
- GVGMLQLDJYHBRK-UHFFFAOYSA-N 3-benzyl-5-[(3-bromo-4-hydroxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CC=2C=CC=CC=2)C(=O)S1 GVGMLQLDJYHBRK-UHFFFAOYSA-N 0.000 claims description 2
- FEADCVBKGKJCIR-UHFFFAOYSA-N 3-ethyl-5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CC)C(=O)SC1=CC1=CC=C(O)C(C(F)(F)F)=C1 FEADCVBKGKJCIR-UHFFFAOYSA-N 0.000 claims description 2
- XLCQBRIJXXDDQD-UHFFFAOYSA-N 4-[5-[(3-bromo-4-hydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]butanenitrile Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CCCC#N)C(=O)S1 XLCQBRIJXXDDQD-UHFFFAOYSA-N 0.000 claims description 2
- BDNQKEQGJWIVMS-UHFFFAOYSA-N 4-[5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]butanenitrile Chemical compound C1=C(C(F)(F)F)C(O)=CC=C1C=C1C(=O)N(CCCC#N)C(=O)S1 BDNQKEQGJWIVMS-UHFFFAOYSA-N 0.000 claims description 2
- HDIIETCZJZHIKL-KQWNVCNZSA-N 4-acetyl-n-[4-[(z)-[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]benzenesulfonamide Chemical compound C1=CC(C(=O)C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1\C=C/1C(=O)N(CC2(C)CCCCC2)C(=O)S\1 HDIIETCZJZHIKL-KQWNVCNZSA-N 0.000 claims description 2
- QODYFOVSALNDFH-UHFFFAOYSA-N 4-chloro-n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]-3-nitrobenzenesulfonamide Chemical compound O=C1SC(=CC=2C=CC(NS(=O)(=O)C=3C=C(C(Cl)=CC=3)[N+]([O-])=O)=CC=2)C(=O)N1CC1(C)CCCCC1 QODYFOVSALNDFH-UHFFFAOYSA-N 0.000 claims description 2
- DEWVIIHDJFWMOI-UHFFFAOYSA-N 4-chloro-n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]benzenesulfonamide Chemical compound O=C1SC(=CC=2C=CC(NS(=O)(=O)C=3C=CC(Cl)=CC=3)=CC=2)C(=O)N1CC1(C)CCCCC1 DEWVIIHDJFWMOI-UHFFFAOYSA-N 0.000 claims description 2
- XJERYLZMJQPPHJ-UHFFFAOYSA-N 4-methyl-n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]benzenesulfonamide Chemical compound C1=CC(C)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1C=C1C(=O)N(CC2(C)CCCCC2)C(=O)S1 XJERYLZMJQPPHJ-UHFFFAOYSA-N 0.000 claims description 2
- XDZKANCKGHBNDJ-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CC2OC3=CC=CC=C3OC2)C(=O)S1 XDZKANCKGHBNDJ-UHFFFAOYSA-N 0.000 claims description 2
- NATWHZXMBGJOIT-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-(3-methylbut-2-enyl)-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CC=C(C)C)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 NATWHZXMBGJOIT-UHFFFAOYSA-N 0.000 claims description 2
- CJKMYSGHYIPVNM-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-(naphthalen-1-ylmethyl)-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CC=2C3=CC=CC=C3C=CC=2)C(=O)S1 CJKMYSGHYIPVNM-UHFFFAOYSA-N 0.000 claims description 2
- PJNMPGGPCDAPRF-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=C(Br)C(O)=CC=2)C(=O)N1CC1(C)CCCCC1 PJNMPGGPCDAPRF-UHFFFAOYSA-N 0.000 claims description 2
- XAPOYCFXEIEWMU-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-[(3-chloro-5-fluorophenyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound C1=C(Br)C(O)=CC=C1C=C1C(=O)N(CC=2C=C(Cl)C=C(F)C=2)C(=O)S1 XAPOYCFXEIEWMU-UHFFFAOYSA-N 0.000 claims description 2
- CIZSBROLZIJTKK-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-[(6,6-dimethyl-1,3-dioxan-4-yl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O1COC(C)(C)CC1CN(C(=O)S1)C(=O)C1=CC1=CC=C(O)C(Br)=C1 CIZSBROLZIJTKK-UHFFFAOYSA-N 0.000 claims description 2
- YEHLUHYDNGXZLL-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-butyl-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CCCC)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 YEHLUHYDNGXZLL-UHFFFAOYSA-N 0.000 claims description 2
- OJYASWBJWRNEOQ-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-ethyl-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CC)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 OJYASWBJWRNEOQ-UHFFFAOYSA-N 0.000 claims description 2
- KITMDYNCRQQJHE-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-pentyl-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CCCCC)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 KITMDYNCRQQJHE-UHFFFAOYSA-N 0.000 claims description 2
- WZNLBFFYKGKGCF-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-propan-2-yl-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(C(C)C)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 WZNLBFFYKGKGCF-UHFFFAOYSA-N 0.000 claims description 2
- UCKMAPXXJBNXBM-UHFFFAOYSA-N 5-[(3-bromo-4-hydroxyphenyl)methylidene]-3-propyl-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CCC)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 UCKMAPXXJBNXBM-UHFFFAOYSA-N 0.000 claims description 2
- JBRKPTJVFBDBTQ-UHFFFAOYSA-N 5-[(4-chlorophenyl)methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=CC(Cl)=CC=2)C(=O)N1CC1(C)CCCCC1 JBRKPTJVFBDBTQ-UHFFFAOYSA-N 0.000 claims description 2
- SFPQNIHJMMNKFQ-UHFFFAOYSA-N 5-[(4-hydroxynaphthalen-1-yl)methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C3=CC=CC=C3C(O)=CC=2)C(=O)N1CC1(C)CCCCC1 SFPQNIHJMMNKFQ-UHFFFAOYSA-N 0.000 claims description 2
- ZEIHTDYXMHCVGJ-UHFFFAOYSA-N 5-[(4-hydroxyphenyl)methylidene]-3-[(1-methylcyclohexyl)methyl]-1,3-thiazolidine-2,4-dione Chemical compound O=C1SC(=CC=2C=CC(O)=CC=2)C(=O)N1CC1(C)CCCCC1 ZEIHTDYXMHCVGJ-UHFFFAOYSA-N 0.000 claims description 2
- LJRDMYPLMBOIFV-UHFFFAOYSA-N 5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-3-(3-methylbut-2-enyl)-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CC=C(C)C)C(=O)SC1=CC1=CC=C(O)C(C(F)(F)F)=C1 LJRDMYPLMBOIFV-UHFFFAOYSA-N 0.000 claims description 2
- CSLBUUVXPNRUAH-UHFFFAOYSA-N 5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-3-propyl-1,3-thiazolidine-2,4-dione Chemical compound O=C1N(CCC)C(=O)SC1=CC1=CC=C(O)C(C(F)(F)F)=C1 CSLBUUVXPNRUAH-UHFFFAOYSA-N 0.000 claims description 2
- LHHVWRCWTFELGF-UHFFFAOYSA-N 6-[5-[(3-bromo-4-hydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-2,2-dimethylhexanenitrile Chemical compound O=C1N(CCCCC(C)(C)C#N)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 LHHVWRCWTFELGF-UHFFFAOYSA-N 0.000 claims description 2
- KBPHERWPHNDMEN-UHFFFAOYSA-N 6-[5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]-2,2-dimethylhexanenitrile Chemical compound O=C1N(CCCCC(C)(C)C#N)C(=O)SC1=CC1=CC=C(O)C(C(F)(F)F)=C1 KBPHERWPHNDMEN-UHFFFAOYSA-N 0.000 claims description 2
- XOHXBGOSXXXKHN-UHFFFAOYSA-N ethyl 4-[5-[(3-bromo-4-hydroxyphenyl)methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]butanoate Chemical compound O=C1N(CCCC(=O)OCC)C(=O)SC1=CC1=CC=C(O)C(Br)=C1 XOHXBGOSXXXKHN-UHFFFAOYSA-N 0.000 claims description 2
- MFYLNYYWNFTIAW-UHFFFAOYSA-N ethyl 4-[5-[[4-hydroxy-3-(trifluoromethyl)phenyl]methylidene]-2,4-dioxo-1,3-thiazolidin-3-yl]butanoate Chemical compound O=C1N(CCCC(=O)OCC)C(=O)SC1=CC1=CC=C(O)C(C(F)(F)F)=C1 MFYLNYYWNFTIAW-UHFFFAOYSA-N 0.000 claims description 2
- YDLHLTAGIFUNRU-UHFFFAOYSA-N methyl 4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C=C1C(=O)N(CC2(C)CCCCC2)C(=O)S1 YDLHLTAGIFUNRU-UHFFFAOYSA-N 0.000 claims description 2
- KAGILWRIPQFLGP-UHFFFAOYSA-N n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]-2-nitrobenzenesulfonamide Chemical compound O=C1SC(=CC=2C=CC(NS(=O)(=O)C=3C(=CC=CC=3)[N+]([O-])=O)=CC=2)C(=O)N1CC1(C)CCCCC1 KAGILWRIPQFLGP-UHFFFAOYSA-N 0.000 claims description 2
- XTDQTKMWPHRIJB-UHFFFAOYSA-N n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1C=C1C(=O)N(CC2(C)CCCCC2)C(=O)S1 XTDQTKMWPHRIJB-UHFFFAOYSA-N 0.000 claims description 2
- NSTPBXVDCGTNSG-UHFFFAOYSA-N n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]cyclohexanecarboxamide Chemical compound O=C1SC(=CC=2C=CC(NC(=O)C3CCCCC3)=CC=2)C(=O)N1CC1(C)CCCCC1 NSTPBXVDCGTNSG-UHFFFAOYSA-N 0.000 claims description 2
- 206010062904 Hormone-refractory prostate cancer Diseases 0.000 claims 4
- 206010005003 Bladder cancer Diseases 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010009944 Colon cancer Diseases 0.000 claims 2
- 208000008839 Kidney Neoplasms Diseases 0.000 claims 2
- 206010033128 Ovarian cancer Diseases 0.000 claims 2
- 206010061535 Ovarian neoplasm Diseases 0.000 claims 2
- 206010038389 Renal cancer Diseases 0.000 claims 2
- 208000007097 Urinary Bladder Neoplasms Diseases 0.000 claims 2
- 201000011199 bladder lymphoma Diseases 0.000 claims 2
- 201000007455 central nervous system cancer Diseases 0.000 claims 2
- 208000029742 colonic neoplasm Diseases 0.000 claims 2
- 201000010982 kidney cancer Diseases 0.000 claims 2
- 208000032839 leukemia Diseases 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims 2
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims 2
- 201000005112 urinary bladder cancer Diseases 0.000 claims 2
- OFKRSPLRXKAZTR-UHFFFAOYSA-N 3,4-dimethoxy-n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]benzenesulfonamide Chemical compound C1=C(OC)C(OC)=CC=C1S(=O)(=O)NC(C=C1)=CC=C1C=C1C(=O)N(CC2(C)CCCCC2)C(=O)S1 OFKRSPLRXKAZTR-UHFFFAOYSA-N 0.000 claims 1
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- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
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- 239000000543 intermediate Substances 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 229910052749 magnesium Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
- 229960003194 meglumine Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- UJFNLIFKTOASIY-UHFFFAOYSA-N methyl 5-[[2-[[2-bromo-4-[(2,4-dioxo-1,3-thiazolidin-5-ylidene)methyl]phenoxy]methyl]-2,5,7,8-tetramethyl-3,4-dihydrochromen-6-yl]oxy]pentanoate Chemical compound C1CC2=C(C)C(OCCCCC(=O)OC)=C(C)C(C)=C2OC1(C)COC(C(=C1)Br)=CC=C1C=C1SC(=O)NC1=O UJFNLIFKTOASIY-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
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- 229940126619 mouse monoclonal antibody Drugs 0.000 description 1
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- XKAUQCAWARWQCA-UHFFFAOYSA-N n-[4-[[3-[(1-methylcyclohexyl)methyl]-2,4-dioxo-1,3-thiazolidin-5-ylidene]methyl]phenyl]methanesulfonamide Chemical compound O=C1SC(=CC=2C=CC(NS(C)(=O)=O)=CC=2)C(=O)N1CC1(C)CCCCC1 XKAUQCAWARWQCA-UHFFFAOYSA-N 0.000 description 1
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
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- 238000012910 preclinical development Methods 0.000 description 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 description 1
- 229960004919 procaine Drugs 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000005267 prostate cell Anatomy 0.000 description 1
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- 230000002797 proteolythic effect Effects 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 230000008685 targeting Effects 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 150000008648 triflates Chemical class 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30860P | 1996-11-13 | ||
| US3086008P | 2008-02-22 | 2008-02-22 | |
| PCT/US2009/034650 WO2009105621A1 (en) | 2008-02-22 | 2009-02-20 | Androgen receptot-ablative agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2437149T3 true ES2437149T3 (es) | 2014-01-09 |
Family
ID=40985920
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09712693.2T Active ES2437149T3 (es) | 2008-02-22 | 2009-02-20 | Agentes supresores del receptor de andrógenos |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US7973062B2 (de) |
| EP (1) | EP2254576B1 (de) |
| CA (1) | CA2716047A1 (de) |
| ES (1) | ES2437149T3 (de) |
| WO (1) | WO2009105621A1 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20100078837A1 (en) * | 2008-09-29 | 2010-04-01 | Pugh Randall B | Apparatus and method for formation of an energized ophthalmic device |
| JP2011057643A (ja) * | 2009-09-14 | 2011-03-24 | Sumitomo Chemical Co Ltd | ３型１７β−ヒドロキシステロイドデヒドロゲナーゼを阻害するための化合物の使用およびそのための医薬組成物 |
| JP2011057644A (ja) * | 2009-09-14 | 2011-03-24 | Sumitomo Chemical Co Ltd | ３型１７β−ヒドロキシステロイドデヒドロゲナーゼを阻害するための化合物の使用およびそのための医薬組成物 |
| CA2777406A1 (en) * | 2009-10-09 | 2011-04-14 | The Ohio State University Research Foundation | Thiazolidinedione energy restriction-mimetic agents |
| CN102078318A (zh) * | 2009-11-27 | 2011-06-01 | 华东理工大学 | 5-取代-2，4-噻唑烷二酮类化合物在制备igf1r功能调节药物中的应用 |
| FR2986231B1 (fr) * | 2012-01-26 | 2014-07-04 | Centre Nat Rech Scient | Derives de thiazolidinedione, leur preparation et leur utilisation dans le traitement des cancers |
| WO2013148994A1 (en) * | 2012-03-28 | 2013-10-03 | The Ohio State University Research Foundation | Glucose transporter inhibitors |
| US12115148B1 (en) | 2024-05-10 | 2024-10-15 | Imam Mohammad Ibn Saud Islamic University | 3-(2-(1,3-dioxoisoindolin-2-yl)ethyl)-5-(2-hydroxy-5-nitrobenzylidene)thiazolidine-2,4-dione as a potential antitumor and apoptotic inducer |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5697277A (en) | 1980-01-07 | 1981-08-05 | Takeda Chem Ind Ltd | Thiazolidine derivative |
| DE69132713D1 (de) | 1990-04-27 | 2001-10-11 | Sankyo Co | Benzylidenthiazolidinderivate, ihre Herstellung und ihre Anwendung als Lipidperoxid-Inhibitoren |
| US6046222A (en) * | 1993-09-15 | 2000-04-04 | Warner-Lambert Company | Use of thiazolidinedione derivatives in the treatment of polycystic ovary syndrome, gestational diabetes and disease states at risk for progressing to noninsulin-dependent diabetes mellitus |
| US5801173A (en) | 1996-05-06 | 1998-09-01 | Dr. Reddy's Research Foundation | Heterocyclic compounds having antidiabetic, hypolipidaemic, antihypertensive properties, process for their preparation and pharmaceutical compositions containing them |
| WO2001016123A1 (en) | 1999-08-31 | 2001-03-08 | Maxia Pharmaceuticals, Inc. | Benzylidene-thiazolidinediones and analogues and their use in the treatment of inflammation |
| US7714005B2 (en) | 2004-12-22 | 2010-05-11 | The Ohio State University Research Foundation | Small molecule Bcl-xL/Bcl-2 binding inhibitors |
| WO2006069217A2 (en) | 2004-12-22 | 2006-06-29 | The Ohio State Research Foundation | Small molecule cyclin d1 ablative agents |
| BRPI0808662B8 (pt) * | 2007-03-07 | 2021-05-25 | Janssen Pharmaceutica Nv | tiazolidinadiona n-alquiladas de fenóxi substituída, seu uso, composição farmacêutica que as compreende e processo para preparar a referida composição farmacêutica |
-
2009
- 2009-02-20 EP EP09712693.2A patent/EP2254576B1/de not_active Not-in-force
- 2009-02-20 US US12/389,759 patent/US7973062B2/en active Active
- 2009-02-20 CA CA2716047A patent/CA2716047A1/en not_active Abandoned
- 2009-02-20 WO PCT/US2009/034650 patent/WO2009105621A1/en not_active Ceased
- 2009-02-20 ES ES09712693.2T patent/ES2437149T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20090291992A1 (en) | 2009-11-26 |
| EP2254576A1 (de) | 2010-12-01 |
| EP2254576B1 (de) | 2013-08-28 |
| US7973062B2 (en) | 2011-07-05 |
| WO2009105621A1 (en) | 2009-08-27 |
| CA2716047A1 (en) | 2009-08-27 |
| EP2254576A4 (de) | 2012-02-01 |
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